(R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonate → (R)-(+)-1-tert. Butoxy-2,6-dimethylheptane

HRID 26790Notes

Reaction equation

HRID 26790 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][C@@H:13]([CH3:20])[CH2:14][O:15][C:16]([CH3:19])([CH3:18])[CH3:17])(=O)=O)=CC=1.[CH2:22]([Mg]Br)[CH:23]([CH3:25])[CH3:24]>>[C:16]([O:15][CH2:14][C@H:13]([CH3:20])[CH2:12][CH2:11][CH2:22][CH:23]([CH3:25])[CH3:24])([CH3:17])([CH3:18])[CH3:19]

Participants

3

Reactant 2

HCID 131710899(R)-(+)-4-tert. butoxy-3-methyl-1butanol p-toluenesulfonateHCID 178418816HCID 178418816, compound

Product 1

HCID 13206259(R)-(+)-1-tert. Butoxy-2,6-dimethylheptaneYield 76%

Procedure

Coupling of (R)-(+)-4-tert. butoxy-3-methyl-1-butanol p-toluene-sulfonate with isobutylmagnesium bromide was carried out using the procedure of Example 47. (R)-(+)-1-tert. Butoxy-2,6-dimethylheptane was obtained in 76% yield as a colorless liquid.

Sources & evidence

ORD record
ord-4bccc77055d84e7c8e74d73e683a10d0
Source dataset
uspto-grants-1979_04
Patent number
US04151205

Reaction notes

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